1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 50897572, compound

HRID 2170606Notes

Reaction equation

HRID 2170606 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14](O)=[O:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[CH2:32][NH2:33].C(N=C=NCCCN(C)C)C>C(Cl)Cl>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH:33][CH2:32][C:25]3[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:24]=3[O:23][CH3:22])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 5972502,4-DimethoxybenzylamineHCID 63749119HCID 63749119, compound

Product 1

HCID 50897572HCID 50897572, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2,4-difluorobenzyl)-1H-indole-5-carboxylic acid (50 mg, 0.17 mmol, 1 equiv) in DCM (2 mL) were added the (2,4-dimethoxyphenyl)methanamine (27 μL, 0.18 mmol, 1.05 equiv) and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (35 mg, 0.18 mmol, 1.05 equiv). The reaction mixture was stirred 2 h at room temperature. The solvent was removed in vacuo. The residue was dissolved in AcOEt and washed with a 0.5 N HCl aqueous solution, a saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuo to afford a beige powder (56 mg, 0.13 mmol, 76%). ESI-MS (m/z): 437 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in AcOEt
  3. washwashed with a 0.5 N HCl aqueous solution
  4. dry with materiala saturated NaHCO3 solution and brine, dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76ae74b83b84411cab5cdfe2ff9e871d
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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